Proacetylenic reactivity of a push-pull buta-1,2,3-triene: New chromophores and supramolecular systems

Yi Lin Wu; Francesca Tancini; W. Bernd Schweizer; Daniela Paunescu; Corinne Boudon; Jean Paul Gisselbrecht; Peter D. Jarowski; Enrico Dalcanale; François Diederich

doi:10.1002/asia.201100997

Proacetylenic reactivity of a push-pull buta-1,2,3-triene: New chromophores and supramolecular systems

Yi Lin Wu, Francesca Tancini, W. Bernd Schweizer, Daniela Paunescu, Corinne Boudon, Jean Paul Gisselbrecht, Peter D. Jarowski, Enrico Dalcanale, François Diederich^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

20 Scopus citations

Abstract

Proacetylenic: An aniline-based donor-acceptor-substituted butatriene exhibits not only cumulene-like dimerization to give a [4]radialene (λ _max=756 nm), but also acetylene-like (proacetylenic) reactivity towards tetracyanoethene, affording via [2+2] cycloaddition- cycloreversion a NIR-absorbing zwitterionic chromophore (λ _max= 825 nm). The cationic charge on the imminium-type nitrogen in the zwitterion is evidenced by host-guest complexation with a tetraphosphonate cavitand.

Original language	English (US)
Pages (from-to)	1185-1190
Number of pages	6
Journal	Chemistry - An Asian Journal
Volume	7
Issue number	6
DOIs	https://doi.org/10.1002/asia.201100997
State	Published - Jun 2012

Keywords

proacetylenic
push-pull chromophore
radialene
self-assembly
zwitterions

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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title = "Proacetylenic reactivity of a push-pull buta-1,2,3-triene: New chromophores and supramolecular systems",

abstract = "Proacetylenic: An aniline-based donor-acceptor-substituted butatriene exhibits not only cumulene-like dimerization to give a [4]radialene (λ max=756 nm), but also acetylene-like (proacetylenic) reactivity towards tetracyanoethene, affording via [2+2] cycloaddition- cycloreversion a NIR-absorbing zwitterionic chromophore (λ max= 825 nm). The cationic charge on the imminium-type nitrogen in the zwitterion is evidenced by host-guest complexation with a tetraphosphonate cavitand.",

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author = "Wu, {Yi Lin} and Francesca Tancini and Schweizer, {W. Bernd} and Daniela Paunescu and Corinne Boudon and Gisselbrecht, {Jean Paul} and Jarowski, {Peter D.} and Enrico Dalcanale and Fran{\c c}ois Diederich",

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volume = "7",

pages = "1185--1190",

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T1 - Proacetylenic reactivity of a push-pull buta-1,2,3-triene

T2 - New chromophores and supramolecular systems

AU - Wu, Yi Lin

AU - Tancini, Francesca

AU - Schweizer, W. Bernd

AU - Paunescu, Daniela

AU - Boudon, Corinne

AU - Gisselbrecht, Jean Paul

AU - Jarowski, Peter D.

AU - Dalcanale, Enrico

AU - Diederich, François

PY - 2012/6

Y1 - 2012/6

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AB - Proacetylenic: An aniline-based donor-acceptor-substituted butatriene exhibits not only cumulene-like dimerization to give a [4]radialene (λ max=756 nm), but also acetylene-like (proacetylenic) reactivity towards tetracyanoethene, affording via [2+2] cycloaddition- cycloreversion a NIR-absorbing zwitterionic chromophore (λ max= 825 nm). The cationic charge on the imminium-type nitrogen in the zwitterion is evidenced by host-guest complexation with a tetraphosphonate cavitand.

KW - proacetylenic

KW - push-pull chromophore

KW - radialene

KW - self-assembly

KW - zwitterions

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Proacetylenic reactivity of a push-pull buta-1,2,3-triene: New chromophores and supramolecular systems

Abstract

Keywords

ASJC Scopus subject areas

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